He is known for his constant in-joking and punning on the intersection between socialist ideologies and computer programming, as well as other fields. For example, his chapter titles such as "Trusted Third Parties" or "Revolutionary Platform" usually have double (or multiple) meanings. A future programmers union is called "Information Workers of the World Wide Web", or the Webblies, a reference to the Industrial Workers of the World, who are nicknamed the Wobblies. The Webblies idea formed a central part of the novel For the Win by Cory Doctorow and MacLeod is acknowledged as coining the term.[7] Doctorow has also used one of MacLeod's references to the singularity as "the rapture for nerds" as the title for his book Rapture of the Nerds. There are also many references to, or puns on, zoology and palaeontology. For example in The Stone Canal the title of the book, and many places described in it, are named after anatomical features of marine invertebrates such as starfish.

The Sky Road (1999; US paperback ISBN 0-8125-7759-0) BSFA Award winner, 1999;[10] Hugo Award nominee, 2001 [11] – represents an 'alternate future' to the second two books, as its events diverge sharply due to a choice made differently by one of the protagonists in the middle of The Stone Canal[12]

The Restoration Game (2010). Per the author, "In The Restoration Game I revisited the fall of the Soviet Union, with a narrator who is at first a piece in a game played by others, and works her way up to becoming to some extent a player, but – as we see when we pull back at the end – is still part of a larger game." [19]

Intrusion (2012): "an Orwellian surveillance society installs sensors on pregnant women to prevent smoking or drinking; and these women also have to take a eugenic “fix” to eliminate genetic anomalies.[19]

Descent (2014):[20] "My genre model for Descent was bloke-lit – that's basically first-person, self-serving, rueful confessional by a youngish man looking back on youthful stupidities... ... Descent is about flying saucers, hidden races, and Antonio Gramsci's concept of passive revolution, all set in a tale of Scottish middle class family life in and after the Great Depression of the 21st Century. Almost mainstream fiction, really."[19]

^"Of the 27, I counted 15 who would give a definite Yes to independence. Only two of the others – Jenni Calder and myself – give a definite No." " Never knowingly understated". The Early Days of A Better Nation. December 19, 2012. Retrieved February 27, 2014.